


Amy Undercover

by Lamguin



Series: Undercover [1]
Category: Brooklyn Nine-Nine (TV)
Genre: Anal Fingering, Extremely Dubious Consent, F/M, Face Slapping, Face-Fucking, Facials, Large Cock, Multi, Naked Female Clothed Male, Oral Sex, Ripping Clothes, Strip Search, Stripping, Undercover, Vaginal Fingering, Voyeurism
Language: English
Status: Completed
Published: 2020-05-07
Updated: 2020-05-08
Packaged: 2021-03-02 22:41:37
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 5
Words: 4,247
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/24054577
Author URL: https://archiveofourown.org/users/Lamguin/pseuds/Lamguin
Summary: Amy goes undercover to recover some stolen diamonds, but it’s more difficult than anticipated.
Relationships: Amy Santiago/Original Male Character(s), Rosa Diaz/Amy Santiago
Series: Undercover [1]
Series URL: https://archiveofourown.org/series/1736152
Comments: 9
Kudos: 38





	1. Chapter 1

“Are you a cop? Cause if you are you have to tell us.”

Amy resisted the urge to roll her eyes “No, I’m not a cop”

“You know man, I don’t think that cops have to tell you they’re cops.” 

“Really?”

“I don’t think so.”

“Then how do we know she’s not a cop?”

“Listen, gentlemen,” Amy cut in, exasperatedly “while this conversation is truly riveting my client does not like to have things done late, so could we hurry this a long.”

One of the men flapped his hand at her and spoke to his two colleagues “Well we can’t just take someone who might be a cop to Him”

This time Amy did roll her eyes in frustration, the longer she was delayed in talking to these idiots, the more chance there was of their boss selling the diamonds she was after. They’d been stolen from a jewellery store a month ago and these three drug dealers had been caught by another undercover operation offering to sell some diamonds which matched the stolen ones.

“Well how can we make sure she isn’t a cop?”

“I’m not sure.”

Amy groaned and decided she needed to take action, if they let the diamonds get away it would look bad on the entire NYPD who would need a scapegoat, which would end up being the 99. So she did the only thing she could think of, slowly walked towards the three bickering men and slid to her knees in the middle of them, causing them to stop speaking and eye her suspiciously, she reached up and started undoing the middle dealers belt, causing him to jerk in shock,

“What’re you doing?”

“Like I said my client doesn’t like delays, and would a cop do this?” The man looked at his companions with a bewildered expression which turned to excitement.

“No, she wouldn’t,” he answered as Amy flipped his sizable cock out of his pants, gently caressing it as it hardened.

“A cop also wouldn’t get her tits out.” He said hopefully, in answer to this Amy cupped his balls and gently squeezed, causing him to groan in pain and stagger slightly.

“Don’t imagine that you are in control here just because I’m on my knees, this is only to convince you to take me to your boss, my tits don’t need to be involved, got it?”

The man nodded frantically and Amy released her grip, placing both hands on his rock hard shaft and starting to rub up and down, from the base of his large head, to his crotch, in circular motions, earning her groans from above, after a few seconds she placed her mouth on his head and began bobbing slightly, not taking much at first, but letting her tongue caress his tip, soon the man tried his luck again, placing a hand on the back of her head, holding her tight bun of hair, in response she allowed her teeth to make contact with his cock, not so much as to hurt, just as a warning and he quickly retracted his hand.

As Amy began taking more and more of the first man's cock into her mouth she had her hands dragged away from his shaft and placed on the cocks to either side, the one on her right fairly small, the one on her left long and thin, she immediately started stroking them, picking up speed rapidly, she wanted this done.

After a few minutes Amy decided she needed to finish this up and forced herself down the cock in front of her, deepthroating it and pressing her nose into the man's crotch, immediately she felt his cock spasm as he orgasmed down her throat, Amy felt relieved that she wouldn’t have to taste it and pulled her mouth off his quickly softening shaft before turning her attention to the second cock, the one on her left.

Almost as soon as her lips wrapped around his thin head the man moaned and Amy felt her mouth filled with the salty taste of jizz, she resisted the urge to gag and swallowed the unpleasant substance, she turned her head to the final cock and as she leaned in it erupted with an orgasm, shooting ropes across her very annoyed looking face.

Amy stood up and was handed some face wipes, as she cleaned herself up she adjusted her light grey suit before speaking.

“So if we’ve cleared that up can you please take me to your Boss?”


	2. Chapter 2

**Summary for the Chapter:**

> Amy has to go through a search before being taken to the boss

Amy stepped out of the car and followed the guys through the parking lot, eventually they reached the stairs and went down, on the lowest floor there was a door with a voltage warning sign on which was unlocked and pushed open to show a ladder, climbing down after the men Amy had expected something like a warehouse, this guy ran one of the biggest burglary rings in the city, he must have somewhere to store everything, but instead they were in what looked like a normal office, despite the lack of windows, with a large desk at one side and a locked door on the other, one of the men with Amy knocked at the door.

After a few seconds of locks being undone a nondescript guy strode through, dressed in what appeared to be a very expensive suit, he was slim and wore glasses, this wasn’t the boss. With him were two very large men with very big guns who closed and locked the door behind them. 

“Who is this pretty girl John?” The suited man grinned lecherously at Amy.

“This is Vanessa Barley sir, she represents someone who is interested in buying something from The Boss.”

“And you checked her out? She’s clean?”

“Yes sir, no connections to law enforcement of any kind.” Amy had to stifle a laugh at John’s complete lie.

“Well, good job.” The man said before turning back to Amy.

“Now Miss Barley, my name is McCallum, anyone who wants to get to the boss has to get past me, my I ask why your client chose to send someone so… delicate to deal on his behalf?”

God she wanted to break his nose, see who’s delicate then.

“My client thought it would be better to send someone more diplomatic.”

“I’m sure you’re well practiced in… diplomacy.” He leered down at her chest.

“My client is a rather impatient man and I don’t relish the thought of coursing him a delay, so if we may proceed?”

“Not so fast Miss Barley, you see, unlike your client, I am a very patient man… I can wait all the time in the world.”

“To do what?” Amy said, raising an eyebrow.

“To ensure that we don’t take anyone to the boss who we shouldn’t.” Amy suppressed the urge to panic.

“He’s not here?”

“Oh, no; this is where we search everyone before we take them to him.”

_ Shit _ Amy though, she could be sure they wouldn’t find the wire or tracker but they might stop her bringing them.

“I assume I have to strip?”

“A very good idea Miss Barley.”

Amy sighed and shrugged off her jacket, handing it to of the waiting men, before unbuckling her belt and pushing her pants down her exquisite legs, she made sure to bend so as to properly show her panty-clad ass, everyone of course stared at it and so didn’t notice as she brought her arm to her face and bit the button with the tracker in it from her blouse sleeve, swallowing it as she knelt to take off her shoes and socks which were also taken from her, before unbuttoning her blouse and unslung it from her shoulders so that she was standing, just in her black underwear in the small, crowded room.

“I’m afraid those too must go” McCallum said, never taking his eyes off of her shapely tits.

Amy sighed but unclipped her bra and stepped out of her panties, handing both away, she stood without covering herself; determined not to show any weakness.

“Now I’m sorry” McCallum said, sounding anything but, “however we must perform a cavity search.”

“Is that really necessary?” Amy asked, her tone the same; bored, slightly impatient but her mouth had gone slightly dry.

“Oh I’m afraid so, but don’t worry we have some decency we will get a woman to perform it.” The rest of the men looked slightly dejected but being able to stare openly at a beautiful naked Latina made up for the disappointment.

McCallum sent one of his men back through the door to get a suitable employee as well as some spare clothes.

“Yours shall be returned to you as soon as you leave.”

“Thank you.” Amy said, acting like she wasn’t naked surrounded by men staring at her, three of whom she’d sucked off less than an hour ago.

A few minutes later the man returned with a bundle of clothes and a very familiar girl in a white crop top and black pants with bushy hair crammed under a hat.

“Ah Ricky Sheets isn’t it?”


	3. Chapter 3

**Summary for the Chapter:**

> Amy is searched by a friend

Amy mentally fought the urge to cover her chest and crotch as the door was closed and locked behind fellow NYPD officer Rosa Diaz in her alter ego as Gun smuggler/ DJ, neither acknowledged the other despite the shock of seeing each other, one completely naked.

Rosa had infiltrated a gun smuggling ring in another attempt to get close to the diamonds and the guy who’d taken them but no one had thought the two operations would overlap like this.

“Miss Sheets, thank you for your assistance, we have an unexpected visitor who we need searched, if it wouldn’t be too much of a bother.”

“No, of course not.” Rosa said in her accented voice, taking the proffered set of rubber gloves and paced towards her friend, fighting the urge to check on her, merely she snapped the gloved on.

“Open your mouth please.” Amy complied without hesitation, when her mouth was open Rosa extended her long fingers in and started to feel around her gums and under her tongue, round the insides of her cheeks and checking each of her teeth, doing a thorough job, Amy wondered at this until she looked over at McCallum and saw that instead of his previous perverted look he was staring intently at Rosa’s hands, the second he noticed her looking he went back to looking at her naked form with a smile but it was clear to her that he wasn’t quite as easily distracted as he wanted her to believe.

It was a good thing they had decided against hiding anything inside her otherwise either she’d be found out or worse Rosa might try to cover it and they’d both be caught out. Amy just hoped that they wouldn’t remember to check her hair, one of her pins hid a mic,

After a slightly uncomfortable few minutes Rosa withdrew her hands and nodded to McCallum before turning Amy, none too gently, and pushing her to the desk, pulling her legs out slightly before kneeling down behind her and starting to probe her tight, puckered asshole which almost caused Amy to squeal but she managed to keep herself under controlled as Rosa pushed deeper and deeper into her anus.

When Rosa finally pulled her digits from her friend's hole she grinned and licked one of the fingers, making exaggerated moans of enjoyment causing the men to laugh, clearly Rosa’s alter ego was friendly with these men and they expected this kind of behaviour from Nicki.

Rosa spun her friend around again and pushed her up so she was sat on the desk and could again see the whole room gazing lustily at her chest, Rosa replicated her previous process but on her friends pussy, making a  _ very _ thorough investigation to the point where she was just fingering her, almost making Amy moan, and causing the men to whoop and make a few dog whistles.

“Now now, Nicki, let's not get carried away” McCallum said with a perverted smile but now that she was looking for it Amy could see some level of annoyance in his eyes.

Rosa finished up her examination and repeated her finger Pickering but this time offered her fingers to the guys in the room who excitedly accepted until McCallum got them to calm down.

Rosa laughed before giving Amy a hand up and a quick spank on her ass “Ok, she’s clean.” Her voice sounded so weird. 

Amy realised what all that show had been about, distraction so everyone would forget about her hair, but as she stepped towards the pile of clothes she was stopped by McCallum’s voice.

“I think Miss Sheets you forgot something?”

“Ah, of course.” Rosa smiled at her faked idiocy and started unpinning Amy’s hair, allowing it to fall, messily down her shoulders, Amy saw the pin with a mic with the others in Rosa’s hand, then it was gone; disappeared into thin air as Rosa dropped them into a waiting hand before running her fingers through her naked colleagues hair, making sure there was nothing there, or at least putting some effort into making it seem that way. When she was done she looked to McCallum for confirmation, he nodded and she stepped away, allowing Amy to pick up the clothes which she was to wear.

A very small, thin black tank top which said “SLUT” in big red letters across the chest and a black thong.

“Are you sure there’s nothing else?” Amy said, exasperatedly.

“I’m afraid you caught us at unawares, Miss Barley” McCallum grinned with his men but behind his perverted expression she could tell he was thinking it’s easier to negotiate with someone wearing such little clothing, she sighed and pulled on the top, as she was pulling up the thong Rosa spoke up.

“If you don’t need me anymore I’ve got some work to do?”

“Of course Miss Sheets, of course” he waved and the door was unlocked, as she passed Amy spanked her ass which was stuck out as she pulled up the underwear.

“That was fun babe, you should give me a call if you ever want a good time.” This earned a round of laughter from the guys and Amy quickly pulled up the thong, she’d felt something be shoved up her asshole.

She had two thoughts in her head as McCallum started to pick up a phone to arrange transport, one that Rosa was very good with her fingers, and two that the mic wouldn’t be too muffled in its current location.


	4. Chapter 4

**Summary for the Chapter:**

> Amy meets the boss and must find a way to locate the missing diamonds

Amy sat uncomfortably in the back of the van, being leered at by armed men when she was dressed in a far too small tank top and thong is something that would make anyone uncomfortable.

The three men who’d brought her to the parking lot had been sent off on another job and McCallum had sent four armed men with her and the driver, three of whom were sitting in the back with her, not even trying to seem inconspicuous in their lustful gazes at her chest.

McCallum had seemed tempted to go himself but Rosa had managed to distract him by engaging him in a conversation about shipments as the group crossed through an underground depot of various vehicles, some being loaded, others unloaded, realising it would be a while he’d sent the van on its way without him, Amy was glad of that, the intense, searching face she’d seen for an instant had spooked her.

Although she couldn’t see out of the van Amy could tell that they’d driven onto a platform which raised up, she assumed into some garage, and now they were surrounded by the hum of New York traffic.

They had been driving for a very long time before the van stopped, after a few moments the doors open in the back and Amy was led to a manhole cover, looking around she didn’t where she was, nor even what part of the city, the alley they had parked in was between two huge tower blocks, offices by the look of it.

The cover was hauled away and three of the men went with Amy down into the foul smelling opening, with the fourth returning to the van with the driver.

Amy was led through a complex tunnel system before they came up to a small steel door which Amy had difficulty squeezing through when it was opened, through the door was a large, low ceilinged area, similar to the parking lot but here there was no vehicles, only people working on various tasks, guns, drugs and money were being shifted around on a multitude of tables, Amy was walked through the area and to a door which was slid open revealing a very small, metal space; she was pushed in and the door slid shut, then the floor started rumbling and she knew she was in an elevator.

Amy readied herself as the elevator continued to climb for what seemed like hours, but eventually it jolted to a stop and the door slid open again, Amy could tell she was in a top floor of a tower block, it was set up like a very nice office, she stepped out of the elevator and stood awkwardly in the empty room, she tried peering out of the window but they were obscured with slats so she couldn’t get a bearing on where she was, she just hoped that the tracker she swallowed was still working.

“The view’s better from over here” came a deep voice from behind her, turning around she saw a man with immaculate hair he was, clean shaven, muscular and quite tall, he was in a suit which was perfectly tailored. He looked like the perfect head of a legitimate company. Which, Amy considered, he probably was, given the office and high floor.

Amy ignored the lewd remark, she liked that her character didn’t make her pretend to enjoy the company of these people.

“Vanessa Barley, I presume?”

“Indeed, may I know your name?”

“I think not, if I don’t get your clients name then he doesn’t get mine.”

“Understandable, of course.”

“Speaking of this mysterious client,” the man said, gesturing to a seat in front of a desk as he poured himself a drink, “What does he want from me, how does he know I have it, and how much is he offering?”

“Around a month ago an amount of diamond jewellery was stolen from a very high class jeweller.”

“And who says I have them?” 

“My client doesn’t tell me how he knows who has what, just that he wants it bought from them.” It felt beyond weird to be having such a serious conversation while her nipples were clearly visible and the word “SLUT” was plastered across her chest.

“Smart man.” He offered her a drink which she refused.

“Well let’s say I did have those particular items, it would make me a lot more money if I cut them down and sold them piece by piece, much safer as well. So I’m sorry however I must decline whatever offer you are prepared to give me.”

“My client is prepared to offer five times the value of the jewellery.”

A look of shock came over the mans face, and he put down his drink, leaning in and looking at Amy’s face rather than her tits for the first time.

“Five times?”

“Indeed.”

His eyes narrowed suddenly.

“Why on earth would he offer so much?”

“He believes they once belonged to his family but they were forced to sell them.”

The man’s expression changed from one of suspicion to one of barely concealed glee, but then his mouth grew into an evil smile.

“Well that certainly takes care of the financial problems however as I mentioned there are still considerable concerns over traceability, I think I need to be convinced to forget them.”

“What are you suggesting?”

“I’m sure what your client intended when he sent someone so… enticing to do business.” 

Amy sighed ,walked around the desk and knelt between his legs as he pulled out a gigantic cock.

“So, convince me.”

  
  



	5. Chapter 5

**Summary for the Chapter:**

> Amy convinces the Boss.

The cock in front of Amy was about a foot long and was very intimidating with a large, angry looking head but she knew she had to do whatever was necessary to ensure they could know where the diamonds were before storming the two sites she’d discovered, so here goes nothing.

She licked the underside of the throbbing member, grasping it with one hand and using her other to fondle the man’s large balls, she kept on like this; slowly licking and kissing the large shaft but she could see the impatience growing in his face and decided that this wasn’t the place for subtly in her technique, so she knelt up slightly and grasped the thick member with both hands and began to jerk it.

While she knew that the faster he came the sooner this was over Amy couldn’t bring herself to attempt fitting the behemoth into her mouth and tried her best to make do without, she rubbed the shaft with circular motions, paying specific attention to the him of his head, for a while she took a hold of the bottom of his cock with one hand and rapidly jerked the rim with her thumb and forefinger, unable to get them fully around it.

Eventually she started to twirl her tongue around the tip, gradually extending down so she was licking around the entirety of his head, at various points placing gentle kisses on his tip and down the shaft but again she could sense him growing impatient and so forced herself to part her lips and take the head into her mouth, she almost gagged when only around half of the head was inside.

She started to Bob her head up and down, suppressing the urge to puke every time the cock hit the back of her throat, eventually she managed to The the whole head in her mouth, holding herself down for a few seconds before coming up for air and jerking the cock rapidly, spreading her saliva down the shaft, she swallowed and prepared to start again.

This time as soon as her lips spread to allow the head back into her mouth she felt a strong hand on the back of her head which immediately forced her down as his hips thrust up, filling her mouth and throat with his huge shaft.

She started choking and sputtering violently, she took her hands away as her face was fucked violently, The man shoving more and more of his cock into her throat, her arms began flailing as she panicked, connecting with his legs and abdomen, He ignored her however and continued thrusting in and out until she found her face pressed into his crotch and he held her there for a few moments before grasping a handful of hair and pulling back violently, yanking her face off of his cock, and shoving her down beside the chair.

Amy started dragging in lungful of rasping air, coughing violently as she did so, finally she managed to get herself under control.

The man had stood up, towering over her bent form, his saliva covered cock protruding from his body.

“Done already?”

“Of course not.” Amy forced a small smile, she had to do this. “It was merely unexpected… shall we get back to it?” Amy said straightening back up so that her mouth was at a level with his huge, dripping cock.

“I can see why your client sent you.” He said, leaning down and placing a kiss on her lips which she returned, feeling slightly sick, then without warning he reached down and ripped open her top, revealing her beautiful tits.

“Very nice,” he said appreciatively, feeling them up before he placed both hands on her head and pressed his head into her unresisting mouth.

The going was easier now that she was prepared for it however she still hated the experience, but managed to keep from choking or losing control of her limbs this time as he brutally pistoned in and out of her mouth. 

Amy wasn’t sure how long he continued, or how long he could go before cumming, at one point someone must’ve entered as she heard the Man speaking, she didn’t hear much but at the end she made out.

“No, I’m afraid this is just business.”

“Are you sure I can’t get some of that.”

“Quite sure, but next time…”

Amy felt mortified that someone else got to witness her degradation but she was a bit preoccupied with trying not to gag , she knew she just had to keep going until he came, and this would all be over.

Thankfully it wasn’t long after the interruption when she felt the Man tense up and heard him moan, he began pulling his cock out of her throat and the first wave of jizz filled her mouth, but he wasn’t done; he removed his member from her mouth entirely and shot many more ropes, covering her face, hair and tits; Amy sat there and took it, trying not to be sick at the taste in her mouth, then suddenly her cheek exploded in sharp pain and her face jerked sideways as she was slapped, hard, causing her to spit out the cum in her mouth.

“That was most convincing, Sgt Santiago.”

Amy froze.

**Notes for the Chapter:**

> This is where I’m leaving this story for now, might revisit it later on.

**Author's Note:**

> Thanks for reading, suggestions and feedback is appreciated


End file.
